N-aryltetrahydrophthalimide compounds

ABSTRACT

N-aryltetrahydrophthalimide compounds of the general formula I ##STR1## where is --S--C(R) 2  --, and a method for controlling undesirble plant growth.

This is a continuation of application Ser. No. 07/761,187, filed Sep. 17, 1991, now U.S. Pat. No, 5,213,605, which is a division of Ser. No. 07/464,639, filed Jan. 5, 1990, now U.S. Pat. No. 5,080,760, which is an FWC of Ser. No. 07/315,128, filed Feb. 24, 1989, abandoned.

The present invention relates to N-phenyltetrahydrophthalimide compounds of the general formula I ##STR2## where the substituents and indices have the following meanings:

n is 0 or 1, R¹ is hydrogen or halogen, Y is --O--, --S--, --CH₂ --, --S--CR⁴ R⁵ --, --O--CR⁴ R⁵ -- or --CH₂ --CR⁴ R⁵ --, R⁴ and R⁵ independently of one another being hydrogen or C₁ -C₃ -alkyl, R² is hydrogen or C₁ -C₃ -alkyl, R³ is a saturated or monounsaturated 5-membered or 6-membered ring which has an oxygen or sulfur atom in the ring and may be monosubstituted to trisubstituted by C₁ -C₃ -alkyl, or R³ is phenyl which is unsubstituted or monosubstituted to trisubstituted by C₁ - or C₂ -alkyl, halogen, methoxy, nitro and/or cyano, and, if n is 0 and Y is --CH₂ --, --CH₂ --CR⁴ R⁵ -- or --S--CR⁴ R⁵ --, R³ may furthermore be hydrogen, C₁ -C₅ -alkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -alkynyl, C₁ -C₄ -haloalkyl, C₃ - or C₄ -haloalkenyl, C₁ - or C₂ -alkoxy-C₁ - or C₂ -alkyl, C₁ - or C₂ -alkoxy-C₁ - or C₂ -alkoxy-C₁ - or C₂ -alkyl or C₁ -C₆ -alkoxycarbonyl-substituted C₁ -C₃ -alkyl.

The present invention furthermore relates to a method for controlling undesirable plant growth and herbicides which contain these compounds.

N-aryl-substituted tetrahydrophthalimides having a herbicidal action are known. For example, EP-A-170 191 describes tetrahydrophthalimides, but their activity is unsatisfactory at low application rates.

It is an object of the present invention to provide appropriately improved tetrahydrophthalimide compounds.

We have found that this object is achieved in that the N-aryltetrahydrophthalimide compounds of the formula I which were defined at the outset have an advantageous herbicidal action, particularly by the postemergence method, and are selective with respect to a number of crops. Where these compounds are capable of forming stereoisomers, the invention relates to all isomers.

The compounds I are obtained, for example, by first reacting an appropriately substituted aniline of the formula II in a conventional manner in an inert organic solvent with an N-alkylating compound Z-(CHR²)_(n) R³ to give the aniline derivative III and then condensing this in an inert organic solvent with 3,4,5,6-tetrahydrophthalic anhydride to give the N-aryltetrahydrophthalimide I. ##STR3##

The radical Z in the alkylating reagent is a nucleophilic leaving group conventionally used in organic chemistry, such as halogen, e.g. chlorine, bromine or iodine, or sulfonyl, such as toluenesulfonyl or mesyl.

The alkylation is carried out in a conventional manner at up to 200° C., preferably from 0° to 150° C., in an aprotic polar solvent (e.g. acetone, acetonitrile or dimethylformamide), in the presence of a base (e.g. potassium carbonate, sodium hydroxide or sodium hydride).

The condensation of the aniline derivative III with 3,4,5,6-tetrahydrophthalic anhydride is carried out in a protic solvent, such as acetic acid, propionic acid or isobutyric acid, or in an aprotic solvent, such as toluene, xylene or dimethylformamide. The reaction is carried out, as a rule, at from 25° to 200° C., preferably from 70° to 140° C. When an aprotic solvent is used, it is advisable to remove the water continuously.

However, the compounds I are also obtained if an amine II is first. condensed with 3,4,5,6-tetrahydrophthalic anhydride to give the N-phenyltetrahydrophthalimide IV, and the latter is then reacted with an N-alkylating compound Z-(CHR²)_(n) R³ to give I. ##STR4##

These reactions are carried out under conditions similar to those described above.

The required compounds II are prepared in a conventional manner: S. Gabriel et al., Chem. Ber. 12 (1879), 600; W. A. Sexton, J. Chem. Soc. 1939, 470; D. R. Shridar et al., Synthesis 1982, 986; Sandmeyer, Chem. Ber. 19 (1888), 2658, and D. R. Shridar et al. Indian. J. Chem. 24B (1985), 1263.

For the use of the compounds I in accordance with regulations, the following radicals are preferred substituents.

Halogen as used above is fluorine, chlorine or bromine, halogen radicals R¹ preferably being fluorine.

Alkyl includes branched and straight-chain radicals, e.g. methyl, ethyl, n-propyl and isopropyl.

The alkenyl and alkynyl radicals may likewise be branched or straight-chain. Examples of alkenyl radicals in formula I are allyl, 2-propenyl, 2-butenyl, 3-butenyl and 2-isobutenyl, in particular allyl and 2-butenyl, and alkynyl radicals are, as a rule, propargyl, 2-butynyl or 3-butynyl.

The five-membered or six-membered heterocyclic ring of the formula I is preferably a hydrogenated or partially hydrogenated furan, thiophene, pyran or thiopyran ring.

Phenyl preferably includes the unsubstituted and monosubstituted derivatives, e.g. chlorophenyl, methylphenyl and methoxyphenyl.

The N-substituted tetrahydrophthalimides are obtainable from 3,4,5,6-tetrahydrophthalic anhydride and an appropriate aniline of the formula III, for example in a solvent at from 20° to 200° C., preferably from 40° to 150° C. Suitable solvents are, for example, lower alkanoic acids, such as glacial acetic acid or propionic acid, or aprotic solvents, such as toluene or xylene, in the presence of an acidic catalyst, for example an aromatic sulfonic acid.

Preferred compounds I are those in which R¹ is hydrogen or fluorine, R⁴ and R⁵ are each hydrogen or methyl, R² is hydrogen and R³ is 2- or 3-tetrahydrofuryl, 2- or 3-tetrahydrothienyl, 2-, 3- or 4-tetrahydropyranyl, 2-, 3- or 4-tetrahydrothiopyranyl, 5,6-dihydro-2H-pyranyl or 5,6-dihydro-2H-thiopyranyl.

Particularly active novel compounds are listed in Tables I, II, IIa, III, IIIa, IV, IVa, V and VI below.

                  TABLE I                                                          ______________________________________                                          ##STR5##                                                                      R.sup.1                                                                              R.sup.2    R.sup.3        R.sup.4                                                                             R.sup.5                                   ______________________________________                                         H     H                                                                                          ##STR6##      H    H                                         F     H                                                                                          ##STR7##      H    H                                         H     CH.sub.3                                                                                   ##STR8##      H    H                                         F     CH.sub.3                                                                                   ##STR9##      H    H                                         H     H                                                                                          ##STR10##     H    H                                         F     H                                                                                          ##STR11##     H    H                                         H     CH.sub.3                                                                                   ##STR12##     H    H                                         F     CH.sub.3                                                                                   ##STR13##     H    H                                         H     H                                                                                          ##STR14##     H    H                                         F     H                                                                                          ##STR15##     H    H                                         H     CH.sub.3                                                                                   ##STR16##     H    H                                         F     CH.sub.3                                                                                   ##STR17##     H    H                                         H     H                                                                                          ##STR18##     H    H                                         F     H                                                                                          ##STR19##     H    H                                         H     CH.sub.3                                                                                   ##STR20##     H    H                                         F     CH.sub.3                                                                                   ##STR21##     H    H                                         H     H                                                                                          ##STR22##     H    H                                         F     H                                                                                          ##STR23##     H    H                                         H     CH.sub.3                                                                                   ##STR24##     H    H                                         F     CH.sub.3                                                                                   ##STR25##     H    H                                         H     H                                                                                          ##STR26##     CH.sub.3                                                                            H                                         F     H                                                                                          ##STR27##     CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR28##     CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR29##     CH.sub.3                                                                            H                                         H     H                                                                                          ##STR30##     CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR31##     CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR32##     CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR33##     CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR34##     H    H                                         F     H                                                                                          ##STR35##     H    H                                         H     CH.sub.3                                                                                   ##STR36##     H    H                                         F     CH.sub.3                                                                                   ##STR37##     H    H                                         H     H                                                                                          ##STR38##     CH.sub.3                                                                            H                                         F     H                                                                                          ##STR39##     CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR40##     CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR41##     CH.sub.3                                                                            H                                         H     H                                                                                          ##STR42##     CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR43##     CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR44##     CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR45##     CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR46##     H    H                                         F     H                                                                                          ##STR47##     H    H                                         H     CH.sub.3                                                                                   ##STR48##     H    H                                         F     CH.sub.3                                                                                   ##STR49##     H    H                                         H     H                                                                                          ##STR50##     CH.sub.3                                                                            H                                         F     H                                                                                          ##STR51##     CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR52##     CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR53##     CH.sub.3                                                                            H                                         H     H                                                                                          ##STR54##     H    H                                         F     H                                                                                          ##STR55##     H    H                                         H     CH.sub.3                                                                                   ##STR56##     H    H                                         F     CH.sub.3                                                                                   ##STR57##     H    H                                         H     H                                                                                          ##STR58##     CH.sub.3                                                                            H                                         F     H                                                                                          ##STR59##     CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR60##     CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR61##     CH.sub.3                                                                            H                                         H     H                                                                                          ##STR62##     CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR63##     CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR64##     CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR65##     CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR66##     H    H                                         F     H                                                                                          ##STR67##     H    H                                         H     CH.sub.3                                                                                   ##STR68##     H    H                                         F     CH.sub.3                                                                                   ##STR69##     H    H                                         H     H                                                                                          ##STR70##     CH.sub.3                                                                            H                                         F     H                                                                                          ##STR71##     CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR72##     CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR73##     CH.sub.3                                                                            H                                         H     H                                                                                          ##STR74##     CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR75##     CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR76##     CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR77##     CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR78##     CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR79##     CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR80##     CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR81##     CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR82##     H    H                                         F     H                                                                                          ##STR83##     H    H                                         H     CH.sub.3                                                                                   ##STR84##     H    H                                         F     CH.sub.3                                                                                   ##STR85##     H    H                                         H     H                                                                                          ##STR86##     CH.sub.3                                                                            H                                         F     H                                                                                          ##STR87##     CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR88##     CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR89##     CH.sub.3                                                                            H                                         H     H                                                                                          ##STR90##     CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR91##     CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR92##     CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR93##     CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR94##     H    H                                         F     H                                                                                          ##STR95##     H    H                                         H     CH.sub.3                                                                                   ##STR96##     H    H                                         F     CH.sub.3                                                                                   ##STR97##     H    H                                         H     H                                                                                          ##STR98##     CH.sub.3                                                                            H                                         F     H                                                                                          ##STR99##     CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR100##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR101##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR102##    H    H                                         F     H                                                                                          ##STR103##    H    H                                         H     CH.sub.3                                                                                   ##STR104##    H    H                                         F     CH.sub.3                                                                                   ##STR105##    H    H                                         H     H                                                                                          ##STR106##    H    H                                         F     H                                                                                          ##STR107##    H    H                                         H     CH.sub.3                                                                                   ##STR108##    H    H                                         F     CH.sub.3                                                                                   ##STR109##    H    H                                         H     H                                                                                          ##STR110##    H    H                                         F     H                                                                                          ##STR111##    H    H                                         H     CH.sub.3                                                                                   ##STR112##    H    H                                         F     CH.sub.3                                                                                   ##STR113##    H    H                                         H     H                                                                                          ##STR114##    H    H                                         F     H                                                                                          ##STR115##    H    H                                         H     CH.sub.3                                                                                   ##STR116##    H    H                                         F     CH.sub.3                                                                                   ##STR117##    H    H                                         H     H                                                                                          ##STR118##    H    H                                         F     H                                                                                          ##STR119##    H    H                                         H     CH.sub.3                                                                                   ##STR120##    H    H                                         F     CH.sub.3                                                                                   ##STR121##    H    H                                         H     H                                                                                          ##STR122##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR123##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR124##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR125##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR126##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR127##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR128##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR129##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR130##    H    H                                         F     H                                                                                          ##STR131##    H    H                                         H     CH.sub.3                                                                                   ##STR132##    H    H                                         F     CH.sub.3                                                                                   ##STR133##    H    H                                         H     H                                                                                          ##STR134##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR135##    CH.sub.3                                                                            H                                         H     CH.sub.3          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                    ##STR140##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR141##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR142##    H    H                                         F     H                                                                                          ##STR143##    H    H                                         H     CH.sub.3                                                                                   ##STR144##    H    H                                         F     CH.sub.3                                                                                   ##STR145##    H    H                                         H     H                                                                                          ##STR146##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR147##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR148##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR149##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR150##    H    H                                         F     H                                                                                          ##STR151##    H    H                                         H     CH.sub.3                                                                                   ##STR152##    H    H                                         F     CH.sub.3                                                                                   ##STR153##    H    H                                         H     H                                                                                          ##STR154##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR155##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR156##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR157##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR158##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR159##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR160##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR161##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR162##    H    H                                         F     H                                                                                          ##STR163##    H    H                                         H     CH.sub.3                                                                                   ##STR164##    H    H                                         F     CH.sub.3                                                                                   ##STR165##    H    H                                         H     H                                                                                          ##STR166##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR167##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR168##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR169##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR170##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR171##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR172##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR173##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR174##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR175##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR176##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR177##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR178##    H    H                                         F     H                                                                                          ##STR179##    H    H                                         H     CH.sub.3                                                                                   ##STR180##    H    H                                         F     CH.sub.3                                                                                   ##STR181##    H    H                                         H     H                                                                                          ##STR182##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR183##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR184##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR185##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR186##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR187##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR188##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR189##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR190##    H    H                                         F     H                                                                                          ##STR191##    H    H                                         H     CH.sub.3                                                                                   ##STR192##    H    H                                         F     CH.sub.3                                                                                   ##STR193##    H    H                                         H     H                                                                                          ##STR194##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR195##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR196##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR197##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR198##    H    H                                         F     H                                                                                          ##STR199##    H    H                                         H     CH.sub.3                                                                                   ##STR200##    H    H                                         F     CH.sub.3                                                                                   ##STR201##    H    H                                         H     H                                                                                          ##STR202##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR203##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR204##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR205##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR206##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR207##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR208##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR209##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR210##    H    H                                         F     H                                                                                          ##STR211##    H    H                                         H     CH.sub.3                                                                                   ##STR212##    H    H                                         F     CH.sub.3                                                                                   ##STR213##    H    H                                         H     H                                                                                          ##STR214##    H    H                                         F     H                                                                                          ##STR215##    H    H                                         H     CH.sub.3                                                                                   ##STR216##    H    H                                         F     CH.sub.3                                                                                   ##STR217##    H    H                                         H     H                                                                                          ##STR218##    H    H                                         F     H                                                                                          ##STR219##    H    H                                         H     CH.sub.3                                                                                   ##STR220##    H    H                                         F     CH.sub.3                                                                                   ##STR221##    H    H                                         ______________________________________                                    

                  TABLE II                                                         ______________________________________                                          ##STR222##                                                                    R.sup.1                                                                              R.sup.2    R.sup.3        R.sup.4                                                                             R.sup.5                                   ______________________________________                                         H     H                                                                                          ##STR223##    H    H                                         F     H                                                                                          ##STR224##    H    H                                         H     CH.sub.3                                                                                   ##STR225##    H    H                                         F     CH.sub.3                                                                                   ##STR226##    H    H                                         H     H                                                                                          ##STR227##    H    H                                         F     H                                                                                          ##STR228##    H    H                                         H     CH.sub.3                                                                                   ##STR229##    H    H                                         F     CH.sub.3                                                                                   ##STR230##    H    H                                         H     H                                                                                          ##STR231##    H    H                                         F     H                                                                                          ##STR232##    H    H                                         H     CH.sub.3                                                                                   ##STR233##    H    H                                         F     CH.sub.3                                                                                   ##STR234##    H    H                                         H     H                                                                                          ##STR235##    H    H                                         F     H                                                                                          ##STR236##    H    H                                         H     CH.sub.3                                                                                   ##STR237##    H    H                                         F     CH.sub.3                                                                                   ##STR238##    H    H                                         H     H                                                                                          ##STR239##    H    H                                         F     H                                                                                          ##STR240##    H    H                                         H     CH.sub.3                                                                                   ##STR241##    H    H                                         F     CH.sub.3                                                                                   ##STR242##    H    H                                         H     H                                                                                          ##STR243##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR244##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR245##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR246##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR247##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR248##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR249##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR250##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR251##    H    H                                         F     H                                                                                          ##STR252##    H    H                                         H     CH.sub.3                                                                                   ##STR253##    H    H                                         F     CH.sub.3                                                                                   ##STR254##    H    H                                         H     H                                                                                          ##STR255##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR256##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR257##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR258##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR259##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR260##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR261##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR262##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR263##    H    H                                         F     H                                                                                          ##STR264##    H    H                                         H     CH.sub.3                                                                                   ##STR265##    H    H                                         F     CH.sub.3                                                                                   ##STR266##    H    H                                         H     H                                                                                          ##STR267##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR268##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR269##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR270##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR271##    H    H                                         F     H                                                                                          ##STR272##    H    H                                         H     CH.sub.3                                                                                   ##STR273##    H    H                                         F     CH.sub.3                                                                                   ##STR274##    H    H                                         H     H                                                                                          ##STR275##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR276##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR277##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR278##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR279##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR280##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR281##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR282##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR283##    H    H                                         F     H                                                                                          ##STR284##    H    H                                         H     CH.sub.3                                                                                   ##STR285##    H    H                                         F     CH.sub.3                                                                                   ##STR286##    H    H                                         H     H                                                                                          ##STR287##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR288##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR289##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR290##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR291##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR292##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR293##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR294##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR295##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR296##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR297##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR298##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR299##    H    H                                         F     H                                                                                          ##STR300##    H    H                                         H     CH.sub.3                                                                                   ##STR301##    H    H                                         F     CH.sub.3                                                                                   ##STR302##    H    H                                         H     H                                                                                          ##STR303##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR304##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR305##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR306##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR307##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR308##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR309##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR310##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR311##    H    H                                         F     H                                                                                          ##STR312##    H    H                                         H     CH.sub.3                                                                                   ##STR313##    H    H                                         F     CH.sub.3                                                                                   ##STR314##    H    H                                         H     H                                                                                          ##STR315##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR316##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR317##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR318##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR319##    H    H                                         F     H                                                                                          ##STR320##    H    H                                         H     CH.sub.3                                                                                   ##STR321##    H    H                                         F     CH.sub.3                                                                                   ##STR322##    H    H                                         H     H                                                                                          ##STR323##    H    H                                         F     H                                                                                          ##STR324##    H    H                                         H     CH.sub.3                                                                                   ##STR325##    H    H                                         F     CH.sub.3                                                                                   ##STR326##    H    H                                         H     H                                                                                          ##STR327##    H    H                                         F     H                                                                                          ##STR328##    H    H                                         H     CH.sub.3                                                                                   ##STR329##    H    H                                         F     CH.sub.3                                                                                   ##STR330##    H    H                                         H     H                                                                                          ##STR331##    H    H                                         F     H                                                                                          ##STR332##    H    H                                         H     CH.sub.3                                                                                   ##STR333##    H    H                                         F     CH.sub.3                                                                                   ##STR334##    H    H                                         H     H                                                                                          ##STR335##    H    H                                         F     H                                                                                          ##STR336##    H    H                                         H     CH.sub.3                                                                                   ##STR337##    H    H                                         F     CH.sub.3                                                                                   ##STR338##    H    H                                         H     H                                                                                          ##STR339##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR340##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR341##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR342##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR343##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR344##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR345##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR346##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR347##    H    H                                         F     H                                                                                          ##STR348##    H    H                                         H     CH.sub.3                                                                                   ##STR349##    H    H                                         F     CH.sub.3                                                                                   ##STR350##    H    H                                         H     H                                                                                          ##STR351##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR352##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR353##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR354##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR355##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR356##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR357##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR358##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR359##    H    H                                         F     H                                                                                          ##STR360##    H    H                                         H     CH.sub.3                                                                                   ##STR361##    H    H                                         F     CH.sub.3                                                                                   ##STR362##    H    H                                         H     H                                                                                          ##STR363##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR364##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR365##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR366##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR367##    H    H                                         F     H                                                                                          ##STR368##    H    H                                         H     CH.sub.3                                                                                   ##STR369##    H    H                                         F     CH.sub.3                                                                                   ##STR370##    H    H                                         H     H                                                                                          ##STR371##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR372##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR373##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR374##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR375##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR376##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR377##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR378##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR379##    H    H                                         F     H                                                                                          ##STR380##    H    H                                         H     CH.sub.3                                                                                   ##STR381##    H    H                                         F     CH.sub.3                                                                                   ##STR382##    H    H                                         H     H                                                                                          ##STR383##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR384##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR385##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR386##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR387##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR388##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR389##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR390##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR391##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR392##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR393##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR394##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR395##    H    H                                         F     H                                                                                          ##STR396##    H    H                                         H     CH.sub.3                                                                                   ##STR397##    H    H                                         F     CH.sub.3                                                                                   ##STR398##    H    H                                         H     H                                                                                          ##STR399##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR400##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR401##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR402##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR403##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR404##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR405##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR406##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR407##    H    H                                         F     H                                                                                          ##STR408##    H    H                                         H     CH.sub.3                                                                                   ##STR409##    H    H                                         F     CH.sub.3                                                                                   ##STR410##    H    H                                         H     H                                                                                          ##STR411##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR412##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR413##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR414##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR415##    H    H                                         F     H                                                                                          ##STR416##    H    H                                         H     CH.sub.3                                                                                   ##STR417##    H    H                                         F     CH.sub.3                                                                                   ##STR418##    H    H                                         H     H                                                                                          ##STR419##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR420##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR421##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR422##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR423##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR424##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR425##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR426##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR427##    H    H                                         F     H                                                                                          ##STR428##    H    H                                         H     CH.sub.3                                                                                   ##STR429##    H    H                                         F     CH.sub.3                                                                                   ##STR430##    H    H                                         H     H                                                                                          ##STR431##    H    H                                         F     H                                                                                          ##STR432##    H    H                                         H     CH.sub.3                                                                                   ##STR433##    H    H                                         F     CH.sub.3                                                                                   ##STR434##    H    H                                         H     H                                                                                          ##STR435##    H    H                                         F     H                                                                                          ##STR436##    H    H                                         H     CH.sub.3                                                                                   ##STR437##    H    H                                         F     CH.sub.3                                                                                   ##STR438##    H    H                                         ______________________________________                                    

                  TABLE IIa                                                        ______________________________________                                          ##STR439##                                                                    R.sup.1  R.sup.4                                                                               R.sup.5    A                                                   ______________________________________                                         H        H      H          H                                                   F        H      H          H                                                   H        CH.sub.3                                                                              H          H                                                   F        CH.sub.3                                                                              H          H                                                   H        H      H          CH.sub.3                                            F        H      H          CH.sub.3                                            H        CH.sub.3                                                                              H          CH.sub.3                                            F        CH.sub.3                                                                              H          CH.sub.3                                            H        H      H          CH.sub.2 CH.sub.3                                   F        H      H          CH.sub.2 CH.sub.3                                   H        CH.sub.3                                                                              H          CH.sub.2 CH.sub.3                                   F        CH.sub.3                                                                              H          CH.sub.2 CH.sub.3                                   H        H      H          CH(CH.sub.3).sub.2                                  F        H      H          CH(CH.sub.3).sub.2                                  H        CH.sub.3                                                                              H          CH(CH.sub.3).sub.2                                  F        CH.sub.3                                                                              H          CH(CH.sub.3).sub.2                                  H        H      H          CH.sub.2 CHCH.sub.2                                 F        H      H          CH.sub.2 CHCH.sub.2                                 H        CH.sub.3                                                                              H          CH.sub.2 CHCH.sub.2                                 F        CH.sub.3                                                                              H          CH.sub.2 CHCH.sub.2                                 H        H      H          CH.sub.2 CHCHCH.sub.3                               F        H      H          CH.sub.2 CHCHCH.sub.3                               H        CH.sub.3                                                                              H          CH.sub.2 CHCHCH.sub.3                               F        CH.sub.3                                                                              H          CH.sub.2 CHCHCH.sub.3                               H        H      H          CH.sub.2 C CH                                       F        H      H          CH.sub.2 C CH                                       H        CH.sub.3                                                                              H          CH.sub.2 C CH                                       F        CH.sub.3                                                                              H          CH.sub.2 C CH                                       H        H      H          CH.sub.2 C CCH.sub.3                                F        H      H          CH.sub.2 C CCH.sub.3                                H        CH.sub.3                                                                              H          CH.sub.2 C CCH.sub.3                                F        CH.sub.3                                                                              H          CH.sub.2 C CCH.sub.3                                H        H      H          CH.sub.2 OCH.sub.3                                  F        H      H          CH.sub.2 OCH.sub. 3                                 H        CH.sub.3                                                                              H          CH.sub.2 OCH.sub.3                                  F        CH.sub.3                                                                              H          CH.sub.2 OCH.sub.3                                  H        H      H          (CH.sub.2).sub.2 OCH.sub.3                          F        H      H          (CH.sub.2).sub.2 OCH.sub.3                          H        CH.sub.3                                                                              H          (CH.sub.2).sub.2 OCH.sub.3                          F        CH.sub.3                                                                              H          (CH.sub.2).sub.2 OCH.sub.3                          H        H      H          CH.sub.2 CO.sub.2 CH.sub.3                          F        H      H          CH.sub.2 CO.sub.2 CH.sub.3                          H        CH.sub.3                                                                              H          CH.sub.2 CO.sub.2 CH.sub.3                          F        CH.sub.3                                                                              H          CH.sub.2 CO.sub.2 CH.sub.3                          H        H      H          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 F        H      H          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 H        CH.sub.3                                                                              H          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 F        CH.sub.3                                                                              H          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 H        H      H          CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        H      H          CH(CH.sub.3)CO.sub.2 CH.sub.3                       H        CH.sub.3                                                                              H          CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        CH.sub.3                                                                              H          CH(CH.sub.3)CO.sub.2 CH.sub.3                       H        H      H          CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              F        H      H          CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              H        CH.sub.3                                                                              H          CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              F        CH.sub.3                                                                              H          CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              H        CH.sub.3                                                                              CH.sub.3   H                                                   F        CH.sub.3                                                                              CH.sub.3   H                                                   H        CH.sub.3                                                                              CH.sub.3   CH.sub.3                                            F        CH.sub.3                                                                              CH.sub.3   CH.sub.3                                            H        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                   F        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                   H        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CHCH.sub.2                                 F        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CHCH.sub.2                                 H        CH.sub.3                                                                              CH.sub.3   CH.sub.2 C CH                                       F        CH.sub.3                                                                              CH.sub.3   CH.sub.2 C CH                                       H        CH.sub.3                                                                              CH.sub.3   (CH.sub.2).sub.2 OCH.sub.3                          F        CH.sub.3                                                                              CH.sub.3   (CH.sub.2).sub.2 OCH.sub.3                          H        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CO.sub.2 CH.sub.3                          F        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CO.sub.2 CH.sub.3                          H        CH.sub.3                                                                              CH.sub.3   CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        CH.sub.3                                                                              CH.sub.3   CH(CH.sub.3)CO.sub.2 CH.sub.3                       ______________________________________                                    

                  TABLE III                                                        ______________________________________                                          ##STR440##                                                                    R.sup.1                                                                              R.sup.2    R.sup.3        R.sup.4                                                                             R.sup.5                                   ______________________________________                                         H     H                                                                                          ##STR441##    H    H                                         F     H                                                                                          ##STR442##    H    H                                         H     CH.sub.3                                                                                   ##STR443##    H    H                                         F     CH.sub.3                                                                                   ##STR444##    H    H                                         H     H                                                                                          ##STR445##    H    H                                         F     H                                                                                          ##STR446##    H    H                                         H     CH.sub.3                                                                                   ##STR447##    H    H                                         F     CH.sub.3                                                                                   ##STR448##    H    H                                         H     H                                                                                          ##STR449##    H    H                                         F     H                                                                                          ##STR450##    H    H                                         H     CH.sub.3                                                                                   ##STR451##    H    H                                         F     CH.sub.3                                                                                   ##STR452##    H    H                                         H     H                                                                                          ##STR453##    H    H                                         F     H                                                                                          ##STR454##    H    H                                         H     CH.sub.3                                                                                   ##STR455##    H    H                                         F     CH.sub.3                                                                                   ##STR456##    H    H                                         H     H                                                                                          ##STR457##    H    H                                         F     H                                                                                          ##STR458##    H    H                                         H     CH.sub.3                                                                                   ##STR459##    H    H                                         F     CH.sub.3                                                                                   ##STR460##    H    H                                         H     H                                                                                          ##STR461##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR462##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR463##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR464##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR465##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR466##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR467##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR468##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR469##    H    H                                         F     H                                                                                          ##STR470##    H    H                                         H     CH.sub.3                                                                                   ##STR471##    H    H                                         F     CH.sub.3                                                                                   ##STR472##    H    H                                         H     H                                                                                          ##STR473##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR474##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR475##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR476##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR477##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR478##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR479##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR480##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR481##    H    H                                         F     H                                                                                          ##STR482##    H    H                                         H     CH.sub.3                                                                                   ##STR483##    H    H                                         F     CH.sub.3                                                                                   ##STR484##    H    H                                         H     H                                                                                          ##STR485##    CH.sub. 3                                                                           H                                         F     H                                                                                          ##STR486##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR487##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR488##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR489##    H    H                                         F     H                                                                                          ##STR490##    H    H                                         H     CH.sub.3                                                                                   ##STR491##    H    H                                         F     CH.sub.3                                                                                   ##STR492##    H    H                                         H     H                                                                                          ##STR493##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR494##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR495##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR496##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR497##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR498##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR499##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR500##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR501##    H    H                                         F     H                                                                                          ##STR502##    H    H                                         H     CH.sub.3                                                                                   ##STR503##    H    H                                         F     CH.sub.3                                                                                   ##STR504##    H    H                                         H     H                                                                                          ##STR505##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR506##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR507##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR508##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR509##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR510##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR511##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR512##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR513##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR514##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR515##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR516##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR517##    H    H                                         F     H                                                                                          ##STR518##    H    H                                         H     CH.sub.3                                                                                   ##STR519##    H    H                                         F     CH.sub.3                                                                                   ##STR520##    H    H                                         H     H                                                                                          ##STR521##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR522##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR523##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR524##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR525##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR526##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR527##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR528##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR529##    H    H                                         F     H                                                                                          ##STR530##    H    H                                         H     CH.sub.3                                                                                   ##STR531##    H    H                                         F     CH.sub.3                                                                                   ##STR532##    H    H                                         H     H                                                                                          ##STR533##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR534##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR535##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR536##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR537##    H    H                                         F     H                                                                                          ##STR538##    H    H                                         H     CH.sub.3                                                                                   ##STR539##    H    H                                         F     CH.sub.3                                                                                   ##STR540##    H    H                                         H     H                                                                                          ##STR541##    H    H                                         F     H                                                                                          ##STR542##    H    H                                         H     CH.sub.3                                                                                   ##STR543##    H    H                                         F     CH.sub.3                                                                                   ##STR544##    H    H                                         H     H                                                                                          ##STR545##    H    H                                         F     H                                                                                          ##STR546##    H    H                                         H     CH.sub.3                                                                                   ##STR547##    H    H                                         F     CH.sub.3                                                                                   ##STR548##    H    H                                         H     H                                                                                          ##STR549##    H    H                                         F     H                                                                                          ##STR550##    H    H                                         H     CH.sub.3                                                                                   ##STR551##    H    H                                         F     CH.sub.3                                                                                   ##STR552##    H    H                                         H     H                                                                                          ##STR553##    H    H                                         F     H                                                                                          ##STR554##    H    H                                         H     CH.sub.3                                                                                   ##STR555##    H    H                                         F     CH.sub.3                                                                                   ##STR556##    H    H                                         H     H                                                                                          ##STR557##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR558##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR559##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR560##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR561##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR562##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR563##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR564##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR565##    H    H                                         F     H                                                                                          ##STR566##    H    H                                         H     CH.sub.3                                                                                   ##STR567##    H    H                                         F     CH.sub.3                                                                                   ##STR568##    H    H                                         H     H                                                                                          ##STR569##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR570##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR571##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR572##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR573##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR574##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR575##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR576##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR577##    H    H                                         F     H                                                                                          ##STR578##    H    H                                         H     CH.sub.3                                                                                   ##STR579##    H    H                                         F     CH.sub.3                                                                                   ##STR580##    H    H                                         H     H                                                                                          ##STR581##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR582##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR583##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR584##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR585##    H    H                                         F     H                                                                                          ##STR586##    H    H                                         H     CH.sub.3                                                                                   ##STR587##    H    H                                         F     CH.sub.3                                                                                   ##STR588##    H    H                                         H     H                                                                                          ##STR589##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR590##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR591##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR592##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR593##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR594##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR595##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR596##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR597##    H    H                                         F     H                                                                                          ##STR598##    H    H                                         H     CH.sub.3                                                                                   ##STR599##    H    H                                         F     CH.sub.3                                                                                   ##STR600##    H    H                                         H     H                                                                                          ##STR601##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR602##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR603##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR604##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR605##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR606##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR607##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR608##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR609##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR610##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR611##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR612##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR613##    H    H                                         F     H                                                                                          ##STR614##    H    H                                         H     CH.sub.3                                                                                   ##STR615##    H    H                                         F     CH.sub.3                                                                                   ##STR616##    H    H                                         H     H                                                                                          ##STR617##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR618##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR619##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR620##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR621##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR622##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR623##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub. 3                                                                                  ##STR624##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR625##    H    H                                         F     H                                                                                          ##STR626##    H    H                                         H     CH.sub.3                                                                                   ##STR627##    H    H                                         F     CH.sub.3                                                                                   ##STR628##    H    H                                         H     H                                                                                          ##STR629##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR630##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR631##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR632##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR633##    H    H                                         F     H                                                                                          ##STR634##    H    H                                         H     CH.sub.3                                                                                   ##STR635##    H    H                                         F     CH.sub.3                                                                                   ##STR636##    H    H                                         H     H                                                                                          ##STR637##    CH.sub.3                                                                            H                                         F     H                                                                                          ##STR638##    CH.sub.3                                                                            H                                         H     CH.sub.3                                                                                   ##STR639##    CH.sub.3                                                                            H                                         F     CH.sub.3                                                                                   ##STR640##    CH.sub.3                                                                            H                                         H     H                                                                                          ##STR641##    CH.sub.3                                                                            CH.sub.3                                  F     H                                                                                          ##STR642##    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3                                                                                   ##STR643##    CH.sub.3                                                                            CH.sub.3                                  F     CH.sub.3                                                                                   ##STR644##    CH.sub.3                                                                            CH.sub.3                                  H     H                                                                                          ##STR645##    H    H                                         F     H                                                                                          ##STR646##    H    H                                         H     CH.sub.3                                                                                   ##STR647##    H    H                                         F     CH.sub.3                                                                                   ##STR648##    H    H                                         H     H                                                                                          ##STR649##    H    H                                         F     H                                                                                          ##STR650##    H    H                                         H     CH.sub.3                                                                                   ##STR651##    H    H                                         F     CH.sub.3                                                                                   ##STR652##    H    H                                         H     H                                                                                          ##STR653##    H    H                                         F     H                                                                                          ##STR654##    H    H                                         H     CH.sub.3                                                                                   ##STR655##    H    H                                         F     CH.sub.3                                                                                   ##STR656##    H    H                                         ______________________________________                                    

                  TABLE IIIa                                                       ______________________________________                                          ##STR657##                                                                    R.sup.1  R.sup.4                                                                               R.sup.5    A                                                   ______________________________________                                         H        H      H          H                                                   F        H      H          H                                                   H        CH.sub.3                                                                              H          H                                                   F        CH.sub.3                                                                              H          H                                                   H        H      H          CH.sub.3                                            F        H      H          CH.sub.3                                            H        CH.sub.3                                                                              H          CH.sub.3                                            F        CH.sub.3                                                                              H          CH.sub.3                                            H        H      H          CH.sub.2 CH.sub.3                                   F        H      H          CH.sub.2 CH.sub.3                                   H        CH.sub.3                                                                              H          CH.sub.2 CH.sub.3                                   F        CH.sub.3                                                                              H          CH.sub.2 CH.sub.3                                   H        H      H          CH(CH.sub.3).sub.2                                  F        H      H          CH(CH.sub.3).sub.2                                  H        CH.sub.3                                                                              H          CH(CH.sub.3).sub.2                                  F        CH.sub.3                                                                              H          CH(CH.sub.3).sub.2                                  H        H      H          CH.sub.2 CHCH.sub.2                                 F        H      H          CH.sub.2 CHCH.sub.2                                 H        CH.sub.3                                                                              H          CH.sub.2 CHCH.sub. 2                                F        CH.sub.3                                                                              H          CH.sub.2 CHCH.sub.2                                 H        H      H          CH.sub.2 CHCHCH.sub.3                               F        H      H          CH.sub.2 CHCHCH.sub.3                               H        CH.sub.3                                                                              H          CH.sub.2 CHCHCH.sub.3                               F        CH.sub.3                                                                              H          CH.sub.2 CHCHCH.sub.3                               H        H      H          CH.sub.2 C CH                                       F        H      H          CH.sub.2 C CH                                       H        CH.sub.3                                                                              H          CH.sub.2 C CH                                       F        CH.sub.3                                                                              H          CH.sub.2 C CH                                       H        H      H          CH.sub.2 C CCH.sub.3                                F        H      H          CH.sub.2 C CCH.sub.3                                H        CH.sub.3                                                                              H          CH.sub.2 C CCH.sub.3                                F        CH.sub.3                                                                              H          CH.sub.2 C CCH.sub.3                                H        H      H          CH.sub.2 OCH.sub.3                                  F        H      H          CH.sub.2 OCH.sub.3                                  H        CH.sub.3                                                                              H          CH.sub.2 OCH.sub.3                                  F        CH.sub.3                                                                              H          CH.sub.2 OCH.sub.3                                  H        H      H          (CH.sub.2).sub.2 OCH.sub.3                          F        H      H          (CH.sub.2).sub.2 OCH.sub.3                          H        CH.sub.3                                                                              H          (CH.sub.2).sub.2 OCH.sub.3                          F        CH.sub.3                                                                              H          (CH.sub.2).sub.2 OCH.sub.3                          H        H      H          CH.sub.2 CO.sub.2 CH.sub.3                          F        H      H          CH.sub.2 CO.sub.2 CH.sub.3                          H        CH.sub.3                                                                              H          CH.sub.2 CO.sub.2 CH.sub.3                          F        CH.sub.3                                                                              H          CH.sub.2 CO.sub.2 CH.sub.3                          H        H      H          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 F        H      H          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 H        CH.sub.3                                                                              H          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 F        CH.sub.3                                                                              H          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 H        H      H          CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        H      H          CH(CH.sub.3)CO.sub.2 CH.sub.3                       H        CH.sub.3                                                                              H          CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        CH.sub.3                                                                              H          CH(CH.sub.3)CO.sub.2 CH.sub.3                       H        H      H          CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              F        H      H          CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              H        CH.sub.3                                                                              H          CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              F        CH.sub.3                                                                              H          CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              H        CH.sub.3                                                                              CH.sub.3   H                                                   F        CH.sub.3                                                                              CH.sub.3   H                                                   H        CH.sub.3                                                                              CH.sub.3   CH.sub.3                                            F        CH.sub.3                                                                              CH.sub.3   CH.sub.3                                            H        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                   F        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                   H        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CHCH.sub.2                                 F        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CHCH.sub.2                                 H        CH.sub.3                                                                              CH.sub.3   CH.sub.2 C CH                                       F        CH.sub.3                                                                              CH.sub.3   CH.sub.2 C CH                                       H        CH.sub.3                                                                              CH.sub.3   (CH.sub.2).sub.2 OCH.sub.3                          F        CH.sub.3                                                                              CH.sub.3   (CH.sub.2).sub.2 OCH.sub.3                          H        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CO.sub.2 CH.sub.3                          F        CH.sub.3                                                                              CH.sub.3   CH.sub.2 CO.sub.2 CH.sub.3                          H        CH.sub.3                                                                              CH.sub.3   CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        CH.sub.3                                                                              CH.sub.3   CH(CH.sub.3)CO.sub.2 CH.sub.3                       ______________________________________                                    

                  TABLE IV                                                         ______________________________________                                          ##STR658##                                                                    R.sup.1  R.sup.2        R.sup.3                                                ______________________________________                                         H        H                                                                                              ##STR659##                                            F        H                                                                                              ##STR660##                                            H        CH.sub.3                                                                                       ##STR661##                                            F        CH.sub.3                                                                                       ##STR662##                                            H        H                                                                                              ##STR663##                                            F        H                                                                                              ##STR664##                                            H        CH.sub.3                                                                                       ##STR665##                                            F        CH.sub.3                                                                                       ##STR666##                                            H        H                                                                                              ##STR667##                                            F        H                                                                                              ##STR668##                                            H        CH.sub.3                                                                                       ##STR669##                                            F        CH.sub.3                                                                                       ##STR670##                                            H        H                                                                                              ##STR671##                                            F        H                                                                                              ##STR672##                                            H        CH.sub.3                                                                                       ##STR673##                                            F        CH.sub.3                                                                                       ##STR674##                                            H        H                                                                                              ##STR675##                                            F        H                                                                                              ##STR676##                                            H        CH.sub.3                                                                                       ##STR677##                                            F        CH.sub.3                                                                                       ##STR678##                                            H        H                                                                                              ##STR679##                                            F        H                                                                                              ##STR680##                                            H        CH.sub.3                                                                                       ##STR681##                                            F        CH.sub.3                                                                                       ##STR682##                                            H        H                                                                                              ##STR683##                                            F        H                                                                                              ##STR684##                                            H        CH.sub.3                                                                                       ##STR685##                                            F        CH.sub.3                                                                                       ##STR686##                                            H        H                                                                                              ##STR687##                                            F        H                                                                                              ##STR688##                                            H        CH.sub.3                                                                                       ##STR689##                                            F        CH.sub.3                                                                                       ##STR690##                                            H        H                                                                                              ##STR691##                                            F        H                                                                                              ##STR692##                                            H        CH.sub.3                                                                                       ##STR693##                                            F        CH.sub.3                                                                                       ##STR694##                                            H        H                                                                                              ##STR695##                                            F        H                                                                                              ##STR696##                                            H        CH.sub.3                                                                                       ##STR697##                                            F        CH.sub.3                                                                                       ##STR698##                                            H        H                                                                                              ##STR699##                                            F        H                                                                                              ##STR700##                                            H        CH.sub.3                                                                                       ##STR701##                                            F        CH.sub.3                                                                                       ##STR702##                                            H        H                                                                                              ##STR703##                                            F        H                                                                                              ##STR704##                                            H        CH.sub.3                                                                                       ##STR705##                                            F        CH.sub.3                                                                                       ##STR706##                                            H        H                                                                                              ##STR707##                                            F        H                                                                                              ##STR708##                                            H        CH.sub.3                                                                                       ##STR709##                                            F        CH.sub.3                                                                                       ##STR710##                                            H        H                                                                                              ##STR711##                                            F        H                                                                                              ##STR712##                                            H        CH.sub.3                                                                                       ##STR713##                                            F        CH.sub.3                                                                                       ##STR714##                                            H        H                                                                                              ##STR715##                                            F        H                                                                                              ##STR716##                                            H        CH.sub.3                                                                                       ##STR717##                                            F        CH.sub.3                                                                                       ##STR718##                                            H        H                                                                                              ##STR719##                                            F        H                                                                                              ##STR720##                                            H        CH.sub.3                                                                                       ##STR721##                                            F        CH.sub.3                                                                                       ##STR722##                                            H        H                                                                                              ##STR723##                                            F        H                                                                                              ##STR724##                                            H        CH.sub.3                                                                                       ##STR725##                                            F        CH.sub.3                                                                                       ##STR726##                                            H        H                                                                                              ##STR727##                                            F        H                                                                                              ##STR728##                                            H        CH.sub.3                                                                                       ##STR729##                                            F        CH.sub.3                                                                                       ##STR730##                                            H        H                                                                                              ##STR731##                                            F        H                                                                                              ##STR732##                                            H        CH.sub.3                                                                                       ##STR733##                                            F        CH.sub.3                                                                                       ##STR734##                                            H        H                                                                                              ##STR735##                                            F        H                                                                                              ##STR736##                                            H        CH.sub.3                                                                                       ##STR737##                                            F        CH.sub.3                                                                                       ##STR738##                                            H        H                                                                                              ##STR739##                                            F        H                                                                                              ##STR740##                                            H        CH.sub.3                                                                                       ##STR741##                                            F        CH.sub.3                                                                                       ##STR742##                                            H        H                                                                                              ##STR743##                                            F        H                                                                                              ##STR744##                                            H        CH.sub.3                                                                                       ##STR745##                                            F        CH.sub.3                                                                                       ##STR746##                                            H        H                                                                                              ##STR747##                                            F        H                                                                                              ##STR748##                                            H        CH.sub.3                                                                                       ##STR749##                                            F        CH.sub.3                                                                                       ##STR750##                                            H        H                                                                                              ##STR751##                                            F        H                                                                                              ##STR752##                                            H        CH.sub.3                                                                                       ##STR753##                                            F        CH.sub.3                                                                                       ##STR754##                                            H        H                                                                                              ##STR755##                                            F        H                                                                                              ##STR756##                                            H        CH.sub.3                                                                                       ##STR757##                                            F        CH.sub.3                                                                                       ##STR758##                                            H        H                                                                                              ##STR759##                                            F        H                                                                                              ##STR760##                                            H        CH.sub.3                                                                                       ##STR761##                                            F        CH.sub.3                                                                                       ##STR762##                                            ______________________________________                                    

                  TABLE IVa                                                        ______________________________________                                          ##STR763##                                                                    R.sup.1         A                                                              ______________________________________                                         H               H                                                              F               H                                                              H               CH.sub.3                                                       F               CH.sub.3                                                       H               CH.sub.2 CH.sub.3                                              F               CH.sub.2 CH.sub.3                                              H               CH(CH.sub.3).sub.2                                             F               CH(CH.sub.3).sub.2                                             H               CH.sub.2 CHCH.sub.2                                            F               CH.sub.2 CHCH.sub.2                                            H               CH.sub.2 CHCHCH.sub.3                                          F               CH.sub.2 CHCHCH.sub.3                                          H               CH.sub.2 C CH                                                  F               CH.sub.2 C CH                                                  H               CH.sub.2 C CCH.sub.3                                           F               CH.sub.2 C CCH.sub.3                                           H               CH.sub.2 OCH.sub.3                                             F               CH.sub.2 OCH.sub.3                                             H               (CH.sub.2).sub.2 OCH.sub.3                                     F               (CH.sub.2).sub.2 OCH.sub.3                                     H               CH.sub.2 CO.sub.2 CH.sub. 3                                    F               CH.sub.2 CO.sub.2 CH.sub.3                                     H               CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                            F               CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                            H               CH(CH.sub.3)CO.sub.2 CH.sub.3                                  F               CH(CH.sub.3)CO.sub.2 CH.sub.3                                  H               CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                         F               CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                         ______________________________________                                    

                  TABLE V                                                          ______________________________________                                          ##STR764##                                                                    R.sup.1  R.sup.2        R.sup.3                                                ______________________________________                                         H        H                                                                                              ##STR765##                                            F        H                                                                                              ##STR766##                                            H        CH.sub.3                                                                                       ##STR767##                                            F        CH.sub.3                                                                                       ##STR768##                                            H        H                                                                                              ##STR769##                                            F        H                                                                                              ##STR770##                                            H        CH.sub.3                                                                                       ##STR771##                                            F        CH.sub.3                                                                                       ##STR772##                                            H        H                                                                                              ##STR773##                                            F        H                                                                                              ##STR774##                                            H        CH.sub.3                                                                                       ##STR775##                                            F        CH.sub.3                                                                                       ##STR776##                                            H        H                                                                                              ##STR777##                                            F        H                                                                                              ##STR778##                                            H        CH.sub.3                                                                                       ##STR779##                                            F        CH.sub.3                                                                                       ##STR780##                                            H        H                                                                                              ##STR781##                                            F        H                                                                                              ##STR782##                                            H        CH.sub.3                                                                                       ##STR783##                                            F        CH.sub.3                                                                                       ##STR784##                                            H        H                                                                                              ##STR785##                                            F        H                                                                                              ##STR786##                                            H        CH.sub.3                                                                                       ##STR787##                                            F        CH.sub.3                                                                                       ##STR788##                                            H        H                                                                                              ##STR789##                                            F        H                                                                                              ##STR790##                                            H        CH.sub.3                                                                                       ##STR791##                                            F        CH.sub.3                                                                                       ##STR792##                                            H        H                                                                                              ##STR793##                                            F        H                                                                                              ##STR794##                                            H        CH.sub.3                                                                                       ##STR795##                                            F        CH.sub.3                                                                                       ##STR796##                                            H        H                                                                                              ##STR797##                                            F        H                                                                                              ##STR798##                                            H        CH.sub.3                                                                                       ##STR799##                                            F        CH.sub.3                                                                                       ##STR800##                                            H        H                                                                                              ##STR801##                                            F        H                                                                                              ##STR802##                                            H        CH.sub.3                                                                                       ##STR803##                                            F        CH.sub.3                                                                                       ##STR804##                                            H        H                                                                                              ##STR805##                                            F        H                                                                                              ##STR806##                                            H        CH.sub.3                                                                                       ##STR807##                                            F        CH.sub.3                                                                                       ##STR808##                                            H        H                                                                                              ##STR809##                                            F        H                                                                                              ##STR810##                                            H        CH.sub.3                                                                                       ##STR811##                                            F        CH.sub.3                                                                                       ##STR812##                                            H        H                                                                                              ##STR813##                                            F        H                                                                                              ##STR814##                                            H        CH.sub.3                                                                                       ##STR815##                                            F        CH.sub.3                                                                                       ##STR816##                                            H        H                                                                                              ##STR817##                                            F        H                                                                                              ##STR818##                                            H        CH.sub.3                                                                                       ##STR819##                                            F        CH.sub.3                                                                                       ##STR820##                                            H        H                                                                                              ##STR821##                                            F        H                                                                                              ##STR822##                                            H        CH.sub.3                                                                                       ##STR823##                                            F        CH.sub.3                                                                                       ##STR824##                                            H        H                                                                                              ##STR825##                                            F        H                                                                                              ##STR826##                                            H        CH.sub.3                                                                                       ##STR827##                                            F        CH.sub.3                                                                                       ##STR828##                                            H        H                                                                                              ##STR829##                                            F        H                                                                                              ##STR830##                                            H        CH.sub.3                                                                                       ##STR831##                                            F        CH.sub.3                                                                                       ##STR832##                                            H        H                                                                                              ##STR833##                                            F        H                                                                                              ##STR834##                                            H        CH.sub.3                                                                                       ##STR835##                                            F        CH.sub.3                                                                                       ##STR836##                                            H        H                                                                                              ##STR837##                                            F        H                                                                                              ##STR838##                                            H        CH.sub.3                                                                                       ##STR839##                                            F        CH.sub.3                                                                                       ##STR840##                                            H        H                                                                                              ##STR841##                                            F        H                                                                                              ##STR842##                                            H        CH.sub.3                                                                                       ##STR843##                                            F        CH.sub.3                                                                                       ##STR844##                                            H        H                                                                                              ##STR845##                                            F        H                                                                                              ##STR846##                                            H        CH.sub.3                                                                                       ##STR847##                                            F        CH.sub.3                                                                                       ##STR848##                                            H        H                                                                                              ##STR849##                                            F        H                                                                                              ##STR850##                                            H        CH.sub.3                                                                                       ##STR851##                                            F        CH.sub.3                                                                                       ##STR852##                                            H        H                                                                                              ##STR853##                                            F        H                                                                                              ##STR854##                                            H        CH.sub.3                                                                                       ##STR855##                                            F        CH.sub.3                                                                                       ##STR856##                                            H        H                                                                                              ##STR857##                                            F        H                                                                                              ##STR858##                                            H        CH.sub.3                                                                                       ##STR859##                                            F        CH.sub.3                                                                                       ##STR860##                                            H        H                                                                                              ##STR861##                                            F        H                                                                                              ##STR862##                                            H        CH.sub.3                                                                                       ##STR863##                                            F        CH.sub.3                                                                                       ##STR864##                                            H        H                                                                                              ##STR865##                                            F        H                                                                                              ##STR866##                                            H        CH.sub.3                                                                                       ##STR867##                                            F        CH.sub.3                                                                                       ##STR868##                                            ______________________________________                                    

                  TABLE VI                                                         ______________________________________                                          ##STR869##                                                                    R.sup.1  R.sup.2        R.sup.3                                                ______________________________________                                         H        H                                                                                              ##STR870##                                            F        H                                                                                              ##STR871##                                            H        CH.sub.3                                                                                       ##STR872##                                            F        CH.sub.3                                                                                       ##STR873##                                            H        H                                                                                              ##STR874##                                            F        H                                                                                              ##STR875##                                            H        CH.sub.3                                                                                       ##STR876##                                            F        CH.sub.3                                                                                       ##STR877##                                            H        H                                                                                              ##STR878##                                            F        H                                                                                              ##STR879##                                            H        CH.sub.3                                                                                       ##STR880##                                            F        CH.sub.3                                                                                       ##STR881##                                            H        H                                                                                              ##STR882##                                            F        H                                                                                              ##STR883##                                            H        CH.sub.3                                                                                       ##STR884##                                            F        CH.sub.3                                                                                       ##STR885##                                            H        H                                                                                              ##STR886##                                            F        H                                                                                              ##STR887##                                            H        CH.sub.3                                                                                       ##STR888##                                            F        CH.sub.3                                                                                       ##STR889##                                            H        H                                                                                              ##STR890##                                            F        H                                                                                              ##STR891##                                            H        CH.sub.3                                                                                       ##STR892##                                            F        CH.sub.3                                                                                       ##STR893##                                            H        H                                                                                              ##STR894##                                            F        H                                                                                              ##STR895##                                            H        CH.sub.3                                                                                       ##STR896##                                            F        CH.sub.3                                                                                       ##STR897##                                            H        H                                                                                              ##STR898##                                            F        H                                                                                              ##STR899##                                            H        CH.sub.3                                                                                       ##STR900##                                            F        CH.sub.3                                                                                       ##STR901##                                            H        H                                                                                              ##STR902##                                            F        H                                                                                              ##STR903##                                            H        CH.sub.3                                                                                       ##STR904##                                            F        CH.sub.3                                                                                       ##STR905##                                            H        H                                                                                              ##STR906##                                            F        H                                                                                              ##STR907##                                            H        CH.sub.3                                                                                       ##STR908##                                            F        CH.sub.3                                                                                       ##STR909##                                            H        H                                                                                              ##STR910##                                            F        H                                                                                              ##STR911##                                            H        CH.sub.3                                                                                       ##STR912##                                            F        CH.sub.3                                                                                       ##STR913##                                            H        H                                                                                              ##STR914##                                            F        H                                                                                              ##STR915##                                            H        CH.sub.3                                                                                       ##STR916##                                            F        CH.sub.3                                                                                       ##STR917##                                            H        H                                                                                              ##STR918##                                            F        H                                                                                              ##STR919##                                            H        CH.sub.3                                                                                       ##STR920##                                            F        CH.sub.3                                                                                       ##STR921##                                            H        H                                                                                              ##STR922##                                            F        H                                                                                              ##STR923##                                            H        CH.sub.3                                                                                       ##STR924##                                            F        CH.sub.3                                                                                       ##STR925##                                            H        H                                                                                              ##STR926##                                            F        H                                                                                              ##STR927##                                            H        CH.sub.3                                                                                       ##STR928##                                            F        CH.sub.3                                                                                       ##STR929##                                            H        H                                                                                              ##STR930##                                            F        H                                                                                              ##STR931##                                            H        CH.sub.3                                                                                       ##STR932##                                            F        CH.sub.3                                                                                       ##STR933##                                            H        H                                                                                              ##STR934##                                            F        H                                                                                              ##STR935##                                            H        CH.sub.3                                                                                       ##STR936##                                            F        CH.sub.3                                                                                       ##STR937##                                            H        H                                                                                              ##STR938##                                            F        H                                                                                              ##STR939##                                            H        CH.sub.3                                                                                       ##STR940##                                            F        CH.sub.3                                                                                       ##STR941##                                            H        H                                                                                              ##STR942##                                            F        H                                                                                              ##STR943##                                            H        CH.sub.3                                                                                       ##STR944##                                            F        CH.sub.3                                                                                       ##STR945##                                            H        H                                                                                              ##STR946##                                            F        H                                                                                              ##STR947##                                            H        CH.sub.3                                                                                       ##STR948##                                            F        CH.sub.3                                                                                       ##STR949##                                            H        H                                                                                              ##STR950##                                            F        H                                                                                              ##STR951##                                            H        CH.sub.3                                                                                       ##STR952##                                            F        CH.sub.3                                                                                       ##STR953##                                            H        H                                                                                              ##STR954##                                            F        H                                                                                              ##STR955##                                            H        CH.sub.3                                                                                       ##STR956##                                            F        CH.sub.3                                                                                       ##STR957##                                            H        H                                                                                              ##STR958##                                            F        H                                                                                              ##STR959##                                            H        CH.sub.3                                                                                       ##STR960##                                            F        CH.sub.3                                                                                       ##STR961##                                            H        H                                                                                              ##STR962##                                            F        H                                                                                              ##STR963##                                            H        CH.sub.3                                                                                       ##STR964##                                            F        CH.sub.3                                                                                       ##STR965##                                            H        H                                                                                              ##STR966##                                            F        H                                                                                              ##STR967##                                            H        CH.sub.3                                                                                       ##STR968##                                            F        CH.sub.3                                                                                       ##STR969##                                            H        H                                                                                              ##STR970##                                            F        H                                                                                              ##STR971##                                            H        CH.sub.3                                                                                       ##STR972##                                            F        CH.sub.3                                                                                       ##STR973##                                            ______________________________________                                    

The N-aryltetrahydrophthalimide compounds I, or herbicidal agents containing them, may be .applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts. and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient.

Examples of formulations are given below.

I. 90 parts by weight of compound no. 1.003 is mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 1.011 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide,-5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

III. 20 parts by weight of compound no. 1.035 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

IV. 20 parts by weight of compound no. 3.059 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

v. 20 parts by weight of compound no. 4.047 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and trituratea in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained containing 0.1% by weight of the active ingredient.

VI. 3 parts by weight of compound no. 1.023 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII. 30 parts by weight of compound no. 1.033 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 20 parts of compound no. 3.067 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

The herbicidal agents, or the active ingredients on which they are based, may be applied pre- or postemergence. If certain crop plants tolerate the active ingredients less well, application techniques may be used in which the herbicidal agents are sprayed from suitable equipment in such a manner that the leaves of sensitive crop plants are if possible not touched, and the agents reach the soil or the unwanted plants growing beneath the crop plants (post-directed, lay-by treatment).

The application rates depend on the objective to be achieved, the time of the year, the plants to be combated and their growth stage, and are from 0.001 to 5.0, preferably 0.01 to 0.5, kg/ha.

In view of the number of application methods available the compounds according to the invention, or agents containing them, may be used in a further large number of crop plants for combating unwanted plants. Examples of such crops are as follows:

    ______________________________________                                         Botanical name       Common name                                               ______________________________________                                         Allium cepa          onions                                                    Ananas comosus       Pineapples                                                Arachis hypogaea     peanuts (groundnuts)                                      Asparagus officinalis                                                                               asparagus                                                 Avena sativa         oats                                                      Beta vulgaris spp. altissima                                                                        sugarbeets                                                Beta vulgaris spp. rapa                                                                             fodder beets                                              Beta vulgaris spp. esculenta                                                                        table beets, red beets                                    Brassica napus var. napus                                                                           rapeseed                                                  Brassica napus var. napobrassica                                                                    swedes                                                    Brassica napus var. rapa                                                                            turnips                                                   Brassica rapa var. silvestris                                                  Camellia sinensis    tea plants                                                Carthamus tinctorius safflower                                                 Carya illinoinensis  pecan trees                                               Citrus limon         lemons                                                    Citrus maxima        grapefruits                                               Citrus reticulata    mandarins                                                 Citrus sinensis      orange trees                                              Coffea arabica (Coffea canephora,                                                                   coffee plants                                             Coffea liberica)                                                               Cucumis melo         melons                                                    Cucumis sativus      cucumbers                                                 Cynodon dactylon     Bermudagrass                                              Daucus carota        carrots                                                   Elais guineensis     oil palms                                                 Fragaria vesca       strawberries                                              Glycine max          soybeans                                                  Gossypium hirsutum (Gossypium                                                                       cotton                                                    arboreum, Gossypium herbaceum,                                                 Gossypium vitifolium)                                                          Helianthus annuus    sunflowers                                                Helianthus tuberosus Jerusalem artichoke                                       Hevea brasiliensis   rubber plants                                             Hordeum vulgare      barley                                                    Humulus lupulus      hops                                                      Ipomoea batatas      sweet potatoes                                            Juglans regia        walnut trees                                              Lactuca sativa       lettuce                                                   Lens culinaris       lentils                                                   Linum usitatissimum  flax                                                      Lycopersicon lycopersicum                                                                           tomatoes                                                  Malus spp.           apple trees                                               Manihot esculenta    cassava                                                   Medicago sativa      alfalfa (lucerne)                                         Mentha piperita      peppermint                                                Musa spp.            banana plants                                             Nicotiana tabacum (N. rustica)                                                                      tobacco                                                   Olea europaea        olive trees                                               Oryza sativa         rice                                                      Phaseolus lunatus    limabeans                                                 Phaseolus mungo      mungbeans                                                 Phaseolus vulgaris   snapbeans, green beans,                                                        dry beans                                                 Pennisetum glaucum   pearl millet                                              Petroselinum crispum spp.                                                                           parsley                                                   tuberosum                                                                      Picea abies          Norway spruce                                             Abies alba           fir trees                                                 Pinus spp.           pine trees                                                Pisum sativum        English peas                                              Prunus avium         cherry trees                                              Prunus domestica     plum trees                                                Prunus dulcis        almond trees                                              Prunus persica       peach trees                                               Pyrus communis       pear trees                                                Ribes sylvestre      redcurrants                                               Ribes uva-crispa     gooseberries                                              Ricinus communis     castor-oil plants                                         Saccharum officinarum                                                                               sugar cane                                                Secale cereale       rye                                                       Sesamum indicum      sesame                                                    Solanum tuberosum    lrish potatoes                                            Sorghum bicolor (s. vulgare)                                                                        sorghum                                                   Sorghum dochna       sorgo                                                     Spinacia oleracea    spinach                                                   Theobroma cacao      cacao plants                                              Trifolium pratense   red clover                                                Triticum aestivum    wheat                                                     Triticum durum       durum wheat                                               Vaccinium corymbosum blueberries                                               Vaccinium vitis-idaea                                                                               cranberries                                               Vicia faba           tick beans                                                Vigna sinensis (V. unguiculata)                                                                     cow peas                                                  Vitis vinifera       grapes                                                    Zea mays             Indian corn, sweet corn,                                                       maize                                                     ______________________________________                                    

To increase the spectrum of action and to achieve synergistic effects, the N-aryltetrahydrophthalimide compounds of the formula I may be mixed and applied together with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable components are diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acids, phenyloxy- or heteroaryloxy-phenylpropionic acids and salts, esters and amides thereof, etc.

It may also be useful to apply the novel compounds of the formula I, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combating pests or phytopathogenic fungi or bacteria. The compounds may also be mixed with solutions of mineral salts used to remedy nutritional or trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

SYNTHESIS EXAMPLES EXAMPLE 1 ##STR974## a) 4.9 g (0.03 mol) of 6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one is introduced into 50 ml of dimethylformamide. At 5° C., 0.79 g (0.033 mol) of sodium hydride is added, and the mixture is stirred for 30 minutes at this temperature. Subsequently, 5.9 g (0.033 mol) of 4-bromomethyltetrahydropyran is added, the mixture is stirred for 3 hours at 60° C., 200 ml of water is added, extraction is carried out twice with methylene chloride, followed by drying and evaporation of the solvent under reduced pressure. There is obtained 5 g (64%) of 4-(tetrahydropyran-4-ylmethyl)-6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one as an oil.

b) 4.5 g (0.017 mol) of the abovementioned aniline and 2.7 g (0.018 mol) of cyclohexene-1,2-dicarboxylic anhydride are stirred for 3 hours at 70° C. in 70 ml of glacial acetic acid. After the mixture has cooled, 100 ml of water is added and the mixture filtered. The precipitate is washed with water and dried. There is obtained 3.5 g (52%) of N-[4-(tetrahydropyran-4-ylmethyl)-3,4-dihydro-2H-1,4-benzoxazin-3-on-6-yl]-3,4,5,6-tetrahydrophthalimide (m.p. 187°-189° C.) (Table 1, No. 1.033).

                  TABLE 1                                                          ______________________________________                                          ##STR975##                    I                                               No.   R.sup.1                                                                               R.sup.2 R.sup.3  R.sup.4                                                                              R.sup.5                                                                             m.p. [°C.]                     ______________________________________                                         1.001 H      H                                                                                       ##STR976##                                                                             H     H                                          1.002 F      H                                                                                       ##STR977##                                                                             H     H                                          1.003 H      H                                                                                       ##STR978##                                                                             H     H    165-166                               1.004 F      H                                                                                       ##STR979##                                                                             H     H    204-206                               1.005 H      H                                                                                       ##STR980##                                                                             CH.sub.3                                                                             H                                          1.006 F      H                                                                                       ##STR981##                                                                             CH.sub.3                                                                             H                                          1.007 H      H                                                                                       ##STR982##                                                                             H     H                                          1.008 F      H                                                                                       ##STR983##                                                                             H     H                                          1.009 H      H                                                                                       ##STR984##                                                                             H     H                                          1.010 F      H                                                                                       ##STR985##                                                                             H     H                                          1.011 H      H                                                                                       ##STR986##                                                                             H     H    140-142                               1.012 F      H                                                                                       ##STR987##                                                                             H     H                                          1.013 H      H                                                                                       ##STR988##                                                                             CH.sub.3                                                                             H                                          1.014 F      H                                                                                       ##STR989##                                                                             CH.sub.3                                                                             H                                          1.015 H      H                                                                                       ##STR990##                                                                             H     H                                          1.016 F      H                                                                                       ##STR991##                                                                             H     H                                          1.017 H      H                                                                                       ##STR992##                                                                             H     H                                          1.018 F      H                                                                                       ##STR993##                                                                             H     H                                          1.019 H      H                                                                                       ##STR994##                                                                             H     H                                          1.020 F      H                                                                                       ##STR995##                                                                             H     H                                          1.021 H      H                                                                                       ##STR996##                                                                             H     H                                          1.022 F      H                                                                                       ##STR997##                                                                             H     H                                          1.023 H      H                                                                                       ##STR998##                                                                             H     H    145-147                               1.024 F      H                                                                                       ##STR999##                                                                             H     H                                          1.025 H      H                                                                                       ##STR1000##                                                                            CH.sub.3                                                                             H                                          1.026 F      H                                                                                       ##STR1001##                                                                            CH.sub.3                                                                             H                                          1.027 H      H                                                                                       ##STR1002##                                                                            H     H    138-140                               1.028 F      H                                                                                       ##STR1003##                                                                            H     H    70 (Zers.)                            1.029 H      H                                                                                       ##STR1004##                                                                            CH.sub.3                                                                             H    145-147                               1.030 F      H                                                                                       ##STR1005##                                                                            CH.sub.3                                                                             H                                          1.031 H      CH.sub.3                                                                                ##STR1006##                                                                            H     H                                          1.032 F      CH.sub.3                                                                                ##STR1007##                                                                            H     H                                          1.033 H      H                                                                                       ##STR1008##                                                                            H     H    187-189                               1.034 F      H                                                                                       ##STR1009##                                                                            H     H                                          1.035 H      H                                                                                       ##STR1010##                                                                            CH.sub.3                                                                             H    150-152                               1.036 F      H                                                                                       ##STR1011##                                                                            CH.sub.3                                                                             H                                          1.037 H      H                                                                                       ##STR1012##                                                                            H     H                                          1.038 F      H                                                                                       ##STR1013##                                                                            H     H                                          1.039 H      H                                                                                       ##STR1014##                                                                            H     H                                          1.040 F      H                                                                                       ##STR1015##                                                                            H     H    178-179                               1.041 H      H                                                                                       ##STR1016##                                                                            CH.sub.3                                                                             H                                          1.042 F      H                                                                                       ##STR1017##                                                                            CH.sub.3                                                                             H                                          1.043 H      H                                                                                       ##STR1018##                                                                            H     H                                          1.044 F      H                                                                                       ##STR1019##                                                                            H     H                                          1.045 H      H                                                                                       ##STR1020##                                                                            H     H                                          1.046 F      H                                                                                       ##STR1021##                                                                            H     H                                          1.047 H      H                                                                                       ##STR1022##                                                                            H     H                                          1.048 F      H                                                                                       ##STR1023##                                                                            H     H                                          1.049 H      H                                                                                       ##STR1024##                                                                            H     H    127-129                               1.050 F      H                                                                                       ##STR1025##                                                                            H     H                                          1.051 H      H                                                                                       ##STR1026##                                                                            H     H                                          1.052 F      H                                                                                       ##STR1027##                                                                            H     H                                          1.053 H      H                                                                                       ##STR1028##                                                                            H     H    178-180                               1.054 F      H                                                                                       ##STR1029##                                                                            H     H                                          1.055 H      H                                                                                       ##STR1030##                                                                            H     H    157-168                               1.056 F      H                                                                                       ##STR1031##                                                                            H     H                                          1.057 H      H                                                                                       ##STR1032##                                                                            H     H    177-178                               1.058 F      H                                                                                       ##STR1033##                                                                            H     H                                          ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR1034##                   I                                               No.   R.sup.1                                                                               R.sup.2 R.sup.3  R.sup.4                                                                              R.sup.5                                                                             m.p. [°C.]                     ______________________________________                                         2.001 H      H                                                                                       ##STR1035##                                                                            H     H                                          2.002 F      H                                                                                       ##STR1036##                                                                            H     H                                          2.003 H      H                                                                                       ##STR1037##                                                                            H     H                                          2.004 F      H                                                                                       ##STR1038##                                                                            H     H                                          2.005 H      H                                                                                       ##STR1039##                                                                            CH.sub.3                                                                             H                                          2.006 F      H                                                                                       ##STR1040##                                                                            CH.sub.3                                                                             H                                          2.007 H      H                                                                                       ##STR1041##                                                                            H     H                                          2.008 F      H                                                                                       ##STR1042##                                                                            H     H                                          2.009 H      H                                                                                       ##STR1043##                                                                            H     H                                          2.010 F      H                                                                                       ##STR1044##                                                                            H     H                                          2.011 H      H                                                                                       ##STR1045##                                                                            H     H                                          2.012 F      H                                                                                       ##STR1046##                                                                            H     H                                          2.013 H      H                                                                                       ##STR1047##                                                                            CH.sub.3                                                                             H                                          2.014 F      H                                                                                       ##STR1048##                                                                            CH.sub.3                                                                             H                                          2.015 H      H                                                                                       ##STR1049##                                                                            H     H                                          2.016 F      H                                                                                       ##STR1050##                                                                            H     H                                          2.017 H      H                                                                                       ##STR1051##                                                                            H     H                                          2.018 F      H                                                                                       ##STR1052##                                                                            H     H                                          2.019 H      H                                                                                       ##STR1053##                                                                            H     H                                          2.020 F      H                                                                                       ##STR1054##                                                                            H     H                                          2.021 H      H                                                                                       ##STR1055##                                                                            H     H                                          2.022 F      H                                                                                       ##STR1056##                                                                            H     H                                          2.023 H      H                                                                                       ##STR1057##                                                                            H     H                                          2.024 F      H                                                                                       ##STR1058##                                                                            H     H                                          2.025 H      H                                                                                       ##STR1059##                                                                            CH.sub.3                                                                             H                                          2.026 F      H                                                                                       ##STR1060##                                                                            CH.sub.3                                                                             H                                          2.027 H      H                                                                                       ##STR1061##                                                                            H     H                                          2.028 F      H                                                                                       ##STR1062##                                                                            H     H                                          2.029 H      H                                                                                       ##STR1063##                                                                            CH.sub.3                                                                             H                                          2.030 F      H                                                                                       ##STR1064##                                                                            CH.sub.3                                                                             H                                          2.031 H      CH.sub.3                                                                                ##STR1065##                                                                            H     H                                          2.032 F      CH.sub.3                                                                                ##STR1066##                                                                            H     H                                          2.033 H      H                                                                                       ##STR1067##                                                                            H     H                                          2.034 F      H                                                                                       ##STR1068##                                                                            H     H                                          2.035 H      H                                                                                       ##STR1069##                                                                            CH.sub.3                                                                             H                                          2.036 F      H                                                                                       ##STR1070##                                                                            CH.sub.3                                                                             H                                          2.037 H      H                                                                                       ##STR1071##                                                                            H     H                                          2.038 F      H                                                                                       ##STR1072##                                                                            H     H                                          2.039 H      H                                                                                       ##STR1073##                                                                            H     H                                          2.040 F      H                                                                                       ##STR1074##                                                                            H     H                                          2.041 H      H                                                                                       ##STR1075##                                                                            CH.sub.3                                                                             H                                          2.042 F      H                                                                                       ##STR1076##                                                                            CH.sub.3                                                                             H                                          2.043 H      H                                                                                       ##STR1077##                                                                            H     H                                          2.044 F      H                                                                                       ##STR1078##                                                                            H     H                                          2.045 H      H                                                                                       ##STR1079##                                                                            H     H                                          2.046 F      H                                                                                       ##STR1080##                                                                            H     H                                          2.047 H      H                                                                                       ##STR1081##                                                                            H     H                                          2.048 F      H                                                                                       ##STR1082##                                                                            H     H                                          2.049 H      H                                                                                       ##STR1083##                                                                            H     H                                          2.050 F      H                                                                                       ##STR1084##                                                                            H     H                                          2.051 H      H                                                                                       ##STR1085##                                                                            H     H                                          2.052 F      H                                                                                       ##STR1086##                                                                            H     H                                          2.053 H      H                                                                                       ##STR1087##                                                                            H     H                                          2.054 F      H                                                                                       ##STR1088##                                                                            H     H                                          2.055 H      H                                                                                       ##STR1089##                                                                            H     H                                          2.056 F      H                                                                                       ##STR1090##                                                                            H     H                                          2.057 H      H                                                                                       ##STR1091##                                                                            H     H                                          2.058 F      H                                                                                       ##STR1092##                                                                            H     H                                          ______________________________________                                    

                  TABLE 2a                                                         ______________________________________                                          ##STR1093##                   I                                               No.   R.sup.1                                                                               A              R.sup.4                                                                              R.sup.5                                                                             m.p. [°C.]                       ______________________________________                                         2.059 H      H              H     H    230-231                                 2.060 F      H              H     H                                            2.061 H      CH.sub.3       H     H                                            2.062 F      CH.sub.3       H     H                                            2.063 H      CH.sub.2 CH.sub.3                                                                             H     H                                            2.064 F      CH.sub.2 CH.sub.3                                                                             H     H                                            2.065 H      CH(CH.sub.3).sub.2                                                                            H     H                                            2.066 F      CH(CH.sub.3).sub.2                                                                            H     H                                            2.067 H      CH.sub.2 CHCH.sub.2                                                                           H     H                                            2.068 F      CH.sub.2 CHCH.sub.2                                                                           H     H                                            2.069 H      CH.sub.2 C CH  H     H    193-194                                 2.070 F      CH.sub.2 C  CH H     H                                            2.071 H      CH.sub.2 OCH.sub.3                                                                            H     H                                            2.072 F      CH.sub.2 OCH.sub.3                                                                            H     H                                            2.073 H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                   H     H                                            2.074 F      CH.sub.2 CH.sub.2 OCH.sub.3                                                                   H     H                                            2.075 H      CH.sub.2 CO.sub.2 CH.sub.3                                                                    H     H                                            2.076 F      CH.sub.2 CO.sub.2 CH.sub.3                                                                    H     H                                            2.077 H      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                           H     H                                            2.078 F      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                           H     H                                            2.079 H      CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                 H     H                                            2.080 F      CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                 H     H                                            2.081 H      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                        H     H                                            2.082 F      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                        H     H                                            2.083 H      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                             H                                            2.084 F      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                             H                                            2.085 H      CH.sub.2 CHCH.sub.2                                                                           CH.sub.3                                                                             H                                            2.086 F      CH.sub.2 CHCH.sub.2                                                                           CH.sub.3                                                                             H                                            2.087 H      CH.sub.2 C CH  CH.sub.3                                                                             H                                            2.088 F      CH.sub.2 C  CH CH.sub.3                                                                             H                                            ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR1094##                   I                                               No.   R.sup.1                                                                               R.sup.2 R.sup.3  R.sup.4                                                                              R.sup.5                                                                             m.p. [°C.]                     ______________________________________                                         3.001 H      H                                                                                       ##STR1095##                                                                            H     H                                          3.002 F      H                                                                                       ##STR1096##                                                                            H     H                                          3.003 H      H                                                                                       ##STR1097##                                                                            H     H                                          3.004 F      H                                                                                       ##STR1098##                                                                            H     H                                          3.005 H      H                                                                                       ##STR1099##                                                                            CH.sub.3                                                                             H                                          3.006 F      H                                                                                       ##STR1100##                                                                            CH.sub.3                                                                             H                                          3.007 H      H                                                                                       ##STR1101##                                                                            H     H                                          3.008 F      H                                                                                       ##STR1102##                                                                            H     H                                          3.009 H      H                                                                                       ##STR1103##                                                                            H     H                                          3.010 F      H                                                                                       ##STR1104##                                                                            H     H                                          3.011 H      H                                                                                       ##STR1105##                                                                            H     H    147-149                               3.012 F      H                                                                                       ##STR1106##                                                                            H     H                                          3.013 H      H                                                                                       ##STR1107##                                                                            CH.sub.3                                                                             H                                          3.014 F      H                                                                                       ##STR1108##                                                                            CH.sub.3                                                                             H                                          3.015 H      H                                                                                       ##STR1109##                                                                            H     H                                          3.016 F      H                                                                                       ##STR1110##                                                                            H     H                                          3.017 H      H                                                                                       ##STR1111##                                                                            H     H                                          3.018 F      H                                                                                       ##STR1112##                                                                            H     H                                          3.019 H      H                                                                                       ##STR1113##                                                                            H     H                                          3.020 F      H                                                                                       ##STR1114##                                                                            H     H                                          3.021 H      H                                                                                       ##STR1115##                                                                            H     H                                          3.022 F      H                                                                                       ##STR1116##                                                                            H     H                                          3.023 H      H                                                                                       ##STR1117##                                                                            H     H                                          3.024 F      H                                                                                       ##STR1118##                                                                            H     H                                          3.025 H      H                                                                                       ##STR1119##                                                                            CH.sub.3                                                                             H                                          3.026 F      H                                                                                       ##STR1120##                                                                            CH.sub.3                                                                             H                                          3.027 H      H                                                                                       ##STR1121##                                                                            H     H    188-190                               3.028 F      H                                                                                       ##STR1122##                                                                            H     H                                          3.029 H      H                                                                                       ##STR1123##                                                                            CH.sub.3                                                                             H                                          3.030 F      H                                                                                       ##STR1124##                                                                            CH.sub.3                                                                             H                                          3.031 H      CH.sub.3                                                                                ##STR1125##                                                                            H     H                                          3.032 F      CH.sub.3                                                                                ##STR1126##                                                                            H     H                                          3.033 H      H                                                                                       ##STR1127##                                                                            H     H                                          3.034 F      H                                                                                       ##STR1128##                                                                            H     H                                          3.035 H      H                                                                                       ##STR1129##                                                                            CH.sub.3                                                                             H                                          3.036 F      H                                                                                       ##STR1130##                                                                            CH.sub.3                                                                             H                                          3.037 H      H                                                                                       ##STR1131##                                                                            H     H                                          3.038 F      H                                                                                       ##STR1132##                                                                            H     H                                          3.039 H      H                                                                                       ##STR1133##                                                                            H     H                                          3.040 F      H                                                                                       ##STR1134##                                                                            H     H                                          3.041 H      H                                                                                       ##STR1135##                                                                            CH.sub.3                                                                             H                                          3.042 F      H                                                                                       ##STR1136##                                                                            CH.sub.3                                                                             H                                          3.043 H      H                                                                                       ##STR1137##                                                                            H     H                                          3.044 F      H                                                                                       ##STR1138##                                                                            H     H                                          3.045 H      H                                                                                       ##STR1139##                                                                            H     H                                          3.046 F      H                                                                                       ##STR1140##                                                                            H     H                                          3.047 H      H                                                                                       ##STR1141##                                                                            H     H                                          3.048 F      H                                                                                       ##STR1142##                                                                            H     H                                          3.049 H      H                                                                                       ##STR1143##                                                                            H     H                                          3.050 F      H                                                                                       ##STR1144##                                                                            H     H                                          3.051 H      H                                                                                       ##STR1145##                                                                            H     H                                          3.052 F      H                                                                                       ##STR1146##                                                                            H     H                                          3.053 H      H                                                                                       ##STR1147##                                                                            H     H                                          3.054 F      H                                                                                       ##STR1148##                                                                            H     H                                          3.055 H      H                                                                                       ##STR1149##                                                                            H     H    173-175                               3.056 F      H                                                                                       ##STR1150##                                                                            H     H                                          3.057 H      H                                                                                       ##STR1151##                                                                            H     H                                          3.058 F      H                                                                                       ##STR1152##                                                                            H     H                                          ______________________________________                                    

                  TABLE 3a                                                         ______________________________________                                          ##STR1153##                   I                                               No.   R.sup.1                                                                               A              R.sup.4                                                                              R.sup.5                                                                             m.p. [°C.]                       ______________________________________                                         3.059 H      H              H     H    237-238                                 3.060 F      H              H     H                                            3.061 H      CH.sub.3       H     H    232-234                                 3.062 F      CH.sub.3       H     H                                            3.063 H      CH.sub.2 CH.sub.3                                                                             H     H                                            3.064 F      CH.sub.2 CH.sub.3                                                                             H     H                                            3.065 H      CH(CH.sub.3).sub.2                                                                            H     H                                            3.066 F      CH(CH.sub.3).sub.2                                                                            H     H                                            3.067 H      CH.sub.2 CHCH.sub.2                                                                           H     H    168-170                                 3.068 F      CH.sub.2 CHCH.sub.2                                                                           H     H                                            3.069 H      CH.sub.2 C CH  H     H    196-198                                 3.070 F      CH.sub.2 C CH  H     H                                            3.071 H      CH.sub.2 OCH.sub.3                                                                            H     H                                            3.072 F      CH.sub.2 OCH.sub.3                                                                            H     H                                            3.073 H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                   H     H                                            3.074 F      CH.sub.2 CH.sub.2 OCH.sub.3                                                                   H     H                                            3.075 H      CH.sub.2 CO.sub.2 CH.sub.3                                                                    H     H                                            3.076 F      CH.sub.2 CO.sub.2 CH.sub.3                                                                    H     H                                            3.077 H      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                           H     H                                            3.078 F      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                           H     H                                            3.079 H      CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                 H     H                                            3.080 F      CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                 H     H                                            3.081 H      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                        H     H                                            3.082 F      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                        H     H                                            3.083 H      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                             H                                            3.084 F      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                             H                                            3.085 H      CH.sub.2 CHCH.sub.2                                                                           CH.sub.3                                                                             H                                            3.086 F      CH.sub.2 CHCH.sub.2                                                                           CH.sub.3                                                                             H                                            3.087 H      CH.sub.2 C CH  CH.sub.3                                                                             H                                            3.088 F      CH.sub.2 C CH  CH.sub.3                                                                             H                                            ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR1154##                   I                                               No.      R.sup.1                                                                               R.sup.2  R.sup.3  m.p. [°C.]                            ______________________________________                                         4.001    H      H                                                                                        ##STR1155##                                          4.002    F      H                                                                                        ##STR1156##                                          4.003    H      H                                                                                        ##STR1157##                                          4.004    F      H                                                                                        ##STR1158##                                          4.005    H      H                                                                                        ##STR1159##                                          4.006    F      H                                                                                        ##STR1160##                                          4.007    H      H                                                                                        ##STR1161##                                          4.008    F      H                                                                                        ##STR1162##                                          4.009    H      H                                                                                        ##STR1163##                                          4.010    F      H                                                                                        ##STR1164##                                          4.011    H      H                                                                                        ##STR1165##                                          4.012    F      H                                                                                        ##STR1166##                                          4.013    H      H                                                                                        ##STR1167##                                          4.014    F      H                                                                                        ##STR1168##                                          4.015    H      H                                                                                        ##STR1169##                                          4.016    H      H                                                                                        ##STR1170##                                          4.017    H      H                                                                                        ##STR1171##                                          4.018    F      H                                                                                        ##STR1172##                                          4.019    H      H                                                                                        ##STR1173##                                          4.020    F      H                                                                                        ##STR1174##                                          4.021    H      H                                                                                        ##STR1175##                                                                            150-152                                      4.022    F      H                                                                                        ##STR1176##                                          4.023    H      CH.sub.3                                                                                 ##STR1177##                                          4.024    F      CH.sub.3                                                                                 ##STR1178##                                          4.025    H      H                                                                                        ##STR1179##                                          4.026    F      H                                                                                        ##STR1180##                                          4.027    H      H                                                                                        ##STR1181##                                          4.028    F      H                                                                                        ##STR1182##                                          4.029    H      H                                                                                        ##STR1183##                                          4.030    F      H                                                                                        ##STR1184##                                          4.031    H      H                                                                                        ##STR1185##                                          4.032    F      H                                                                                        ##STR1186##                                          4.033    H      H                                                                                        ##STR1187##                                          4.034    F      H                                                                                        ##STR1188##                                          4.035    H      H                                                                                        ##STR1189##                                          4.036    F      H                                                                                        ##STR1190##                                          4.037    H      H                                                                                        ##STR1191##                                          4.038    F      H                                                                                        ##STR1192##                                          4.039    H      H                                                                                        ##STR1193##                                          4.040    F      H                                                                                        ##STR1194##                                          4.041    H      H                                                                                        ##STR1195##                                          4.042    F      H                                                                                        ##STR1196##                                          4.043    H      H                                                                                        ##STR1197##                                          4.044    F      H                                                                                        ##STR1198##                                          4.045    H      H                                                                                        ##STR1199##                                          4.046    F      H                                                                                        ##STR1200##                                          ______________________________________                                    

                  TABLE 4a                                                         ______________________________________                                          ##STR1201##                   I                                               No.    R.sup.1   A              m.p. [°C.]                              ______________________________________                                         4.047  H         H              140-142                                        4.048  F         H                                                             4.049  H         CH.sub.3       205-207                                        4.050  F         CH.sub.3                                                      4.051  H         CH.sub.2 CH.sub.3                                             4.052  F         CH.sub.2 CH.sub.3                                             4.053  H         CH(CH.sub.3).sub.2                                            4.054  F         CH(CH.sub.3).sub.2                                            4.055  H         CH.sub.2 CHCH.sub.2                                           4.056  F         CH.sub.2 CHCH.sub.2                                           4.057  H         CH.sub.2 C CH                                                 4.058  F         CH.sub.2 C CH                                                 4.059  H         CH.sub.2 OCH.sub.3                                            4.060  F         CH.sub.2 OCH.sub.3                                            4.061  H         CH.sub.2 CH.sub.2 OCH.sub.3                                   4.062  F         CH.sub.2 CH.sub.2 OCH.sub.3                                   4.063  H         CH.sub.2 CO.sub.2 CH.sub. 3                                   4.064  F         CH.sub.2 CO.sub.2 CH.sub.3                                    4.065  H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                           4.066  F         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                           4.067  H         CH(CH.sub.3)CO.sub.2 CH.sub.3                                 4.068  F         CH(CH.sub.3)CO.sub.2 CH.sub.3                                 4.069  H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                        4.070  F         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                        ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR1202##                   I                                               No.      R.sup.1                                                                               R.sup.2  R.sup.3  m.p. [°C.]                            ______________________________________                                         5.001    H      H                                                                                        ##STR1203##                                          5.002    F      H                                                                                        ##STR1204##                                          5.003    H      H                                                                                        ##STR1205##                                          5.004    F      H                                                                                        ##STR1206##                                          5.005    H      H                                                                                        ##STR1207##                                          5.006    F      H                                                                                        ##STR1208##                                          5.007    H      H                                                                                        ##STR1209##                                          5.008    F      H                                                                                        ##STR1210##                                          5.009    H      H                                                                                        ##STR1211##                                                                            147-151                                      5.010    F      H                                                                                        ##STR1212##                                          5.011    H      H                                                                                        ##STR1213##                                          5.012    F      H                                                                                        ##STR1214##                                          5.013    H      H                                                                                        ##STR1215##                                          5.014    F      H                                                                                        ##STR1216##                                          5.015    H      H                                                                                        ##STR1217##                                          5.016    F      H                                                                                        ##STR1218##                                          5.017    H      H                                                                                        ##STR1219##                                          5.018    F      H                                                                                        ##STR1220##                                          5.019    H      H                                                                                        ##STR1221##                                                                            133-135                                      5.020    F      H                                                                                        ##STR1222##                                          5.021    H      H                                                                                        ##STR1223##                                                                            167-169                                      5.022    F      H                                                                                        ##STR1224##                                          5.023    H      CH.sub.3                                                                                 ##STR1225##                                          5.024    F      CH.sub.3                                                                                 ##STR1226##                                          5.025    H      H                                                                                        ##STR1227##                                          5.026    F      H                                                                                        ##STR1228##                                          5.027    H      H                                                                                        ##STR1229##                                          5.028    F      H                                                                                        ##STR1230##                                          5.029    H      H                                                                                        ##STR1231##                                          5.030    F      H                                                                                        ##STR1232##                                          5.031    H      H                                                                                        ##STR1233##                                          5.032    F      H                                                                                        ##STR1234##                                          5.033    H      H                                                                                        ##STR1235##                                          5.034    F      H                                                                                        ##STR1236##                                          5.035    H      H                                                                                        ##STR1237##                                          5.036    F      H                                                                                        ##STR1238##                                          5.037    H      H                                                                                        ##STR1239##                                          5.038    F      H                                                                                        ##STR1240##                                          5.039    H      H                                                                                        ##STR1241##                                          5.040    F      H                                                                                        ##STR1242##                                          5.041    H      H                                                                                        ##STR1243##                                                                            206-207                                      5.042    F      H                                                                                        ##STR1244##                                          5.043    H      H                                                                                        ##STR1245##                                          5.044    F      H                                                                                        ##STR1246##                                          5.045    H      H                                                                                        ##STR1247##                                          5.046    F      H                                                                                        ##STR1248##                                          ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR1249##                   I                                               No.      R.sup.1                                                                               R.sup.2  R.sup.3  m.p. [°C.]                            ______________________________________                                         6.001    H      H                                                                                        ##STR1250##                                          6.002    F      H                                                                                        ##STR1251##                                          6.003    H      H                                                                                        ##STR1252##                                          6.004    F      H                                                                                        ##STR1253##                                          6.005    H      H                                                                                        ##STR1254##                                          6.006    F      H                                                                                        ##STR1255##                                          6.007    H      H                                                                                        ##STR1256##                                          6.008    F      H                                                                                        ##STR1257##                                          6.009    H      H                                                                                        ##STR1258##                                          6.010    F      H                                                                                        ##STR1259##                                          6.011    H      H                                                                                        ##STR1260##                                          6.012    F      H                                                                                        ##STR1261##                                          6.013    H      H                                                                                        ##STR1262##                                          6.014    F      H                                                                                        ##STR1263##                                          6.015    H      H                                                                                        ##STR1264##                                          6.016    F      H                                                                                        ##STR1265##                                          6.017    H      H                                                                                        ##STR1266##                                          6.018    F      H                                                                                        ##STR1267##                                          6.019    H      H                                                                                        ##STR1268##                                          6.020    F      H                                                                                        ##STR1269##                                          6.021    H      H                                                                                        ##STR1270##                                          6.022    F      H                                                                                        ##STR1271##                                          6.023    H      CH.sub.3                                                                                 ##STR1272##                                          6.024    F      CH.sub.3                                                                                 ##STR1273##                                          6.025    H      H                                                                                        ##STR1274##                                          6.026    F      H                                                                                        ##STR1275##                                          6.027    H      H                                                                                        ##STR1276##                                          6.028    F      H                                                                                        ##STR1277##                                          6.029    H      H                                                                                        ##STR1278##                                          6.030    F      H                                                                                        ##STR1279##                                                                            187-189                                      6.031    H      H                                                                                        ##STR1280##                                          6.032    F      H                                                                                        ##STR1281##                                          6.033    H      H                                                                                        ##STR1282##                                          6.034    F      H                                                                                        ##STR1283##                                          6.035    H      H                                                                                        ##STR1284##                                          6.036    F      H                                                                                        ##STR1285##                                          6.037    H      H                                                                                        ##STR1286##                                          6.038    F      H                                                                                        ##STR1287##                                          6.039    H      H                                                                                        ##STR1288##                                          6.040    F      H                                                                                        ##STR1289##                                          6.041    H      H                                                                                        ##STR1290##                                          6.042    F      H                                                                                        ##STR1291##                                          6.043    H      H                                                                                        ##STR1292##                                          6.044    F      H                                                                                        ##STR1293##                                          6.045    H      H                                                                                        ##STR1294##                                          6.046    F      H                                                                                        ##STR1295##                                          ______________________________________                                    

USE EXAMPLES

The action of the N-aryltetrahydrophthalimide compounds of the formula I on plant growth is demonstrated by the following greenhouse experiments:

The vessels employed were plastic flowerpots having a volume of 300 cm³ and filled with a sandy loam containing about 3.0% humus. The seeds of the test plants were sown separately, according to species.

For the postemergence treatment, either plants which had been sown in the pots and grown there were selected, or they were cultivated separately as seedlings and transplanted to the pots a few days before being treated.

Depending on growth form, the plants were grown to a height of from 3 to 15 cm before being treated with the active ingredients which were suspended or emulsified in water and sprayed through finely distributing nozzles. The application rates for postemergence treatment were 0.06 and 0.125 kg of active ingredient per hectare.

The pots were set up in the greenhouse, species from warmer climates in warmer areas (20° to 35° C.) and species from moderate climates at 10° to 20° C. The experiments were run for from 2 to 4 weeks. During this time the plants were tended and their reactions to the various treatments assessed.

The assessment scale was 0 to 100, 100 denoting nonemergence or complete destruction of at least the visible plant parts, and 0 denoting no damage or normal growth.

The plants used in the greenhouse experiments were: Amaranthus retroflexus, Galium aparine, Stellaria media, Veronica spp., Oryza sativa, Solanum nigrum, and Triticum aestivum.

The compounds 1.027 and 1.029, applied postemergence at rates of 0.06 and 0.125 kg/ha, gave excellent control of unwanted broadleaved plants, and were well tolerated by rice and wheat. Compound 3.067, applied postemergence at a rate of 0.06 kg/ha, combated unwanted broadleaved plants without causing any appreciable damage to rice. 

We claim:
 1. An N-aryltetrahydrophthalimide compound of the formula I ##STR1296## wherein the substitutents and indices have the following meanings: R¹ is hydrogen or halogen, Y is -SCR⁴ R⁵ -, R⁵ -, R⁴ and R⁵ independently of one another being hydrogen or C₁ -C₃ -alkyl, R³ is hydrogen, C₁ -C₅ -alkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -alkynyl, C₁ -C₄ -haloalkyl, C₃ - or C₄ -haloalkenyl, C₁ - or C₂ -alkoxy-C₁ - or C₂ -alkyl, C₁ or C₂ -alkoxy-C₁ -, C₂ -alkoxy-C₁ - or C₂ -alkyl, or C₁ -C₄ -alkoxycarbonyl-substituted C₁ -C₃ -alkyl.
 2. A herbicide containing a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I as defined in claim 1 and inert additives.
 3. A herbicide containing a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I as defined in claim 1 and further active constituents.
 4. A method for controlling undesirable plant growth, wherein the undesirable plants and their habitat, are treated with a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I, as defined in claim
 1. 